A girl (21) recently confessed her love for me, and she’s a nice girl, but she’s not a virgin. I approach all possible romantic relationships very seriously with the intent of marriage, and I don’t know whether I should proceed here. She’s started becoming more religious, but I don’t know if it’s for me or for G-d. What are the Halachik ramifications for her? what does the tradition say regarding these kinds of matters? What do secular studies say about these kinds of marriages? There’s a certain amount of disgust in knowing that another man (that she wasn’t married to) has been in her, is that warranted/reasonable? Is that a reason to reject her? I need advice and wisdom regarding this, thank you whoever takes the time to answer this.
Sounds like this couple needs to talk to a competent rabbi, and probably a relationship therapist.
Let's call this three issues:
A.) There's a mismatch between the religious upbringing of the pair.
Just something they need to be aware of, and plan through. If one says but that's how my very-kosher family always did it, what will the other say? Is one of them currently at a different level of observance? How do they intend to navigate such issues?
B.) It's possible one side is taking on more religious practice solely out of interest in the partner.
I mean there's no law about this, but if it's not sincere, that's just not a recipe for a good relationship. These conversations come up a lot with conversions; one rabbi heard a woman say "I came to Judaism through my boyfriend, not because of my boyfriend"; he felt that was reasonable. A conversion beit din would typically ask -- suppose the Jewish partner suddenly wasn't in the picture; would you continue your interest in Judaism?
C.) One side's been "a good teenager", while the other hasn't.
Really it's about what the couple works out for themselves. There's no "thou shalt / thou shalt not" about this. (Unless he's a kohen and she had a non-Jewish boyfriend...). If one side really can't get over this, then it's not a good match because they can't get over it. If they can, that's fine too. There are plenty of solidly happy, religious couples where one had less-religious past, and all that it entails. Okay at some point if everything proceeds, there will be questions about exactly what wording to put in the ketubah, and then what exactly should be pronounced out-loud ... but those are details that can be worked out.